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325058

Sigma-Aldrich

(S)-(+)-3-Bromo-2-methyl-1-propanol

97%

Synonym(s):

(2S)-3-Bromo-2-methyl-1-propanol, (S)-3-Bromo-2-methylpropan-1-ol, (S)-3-Hydroxy-2-methylpropyl bromide

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About This Item

Linear Formula:
BrCH2CH(CH3)CH2OH
CAS Number:
98244-48-5
Molecular Weight:
153.02
Beilstein:
4738280
MDL number:
MFCD00064575
UNSPSC Code:
12352101
PubChem Substance ID:
24859484
NACRES:
NA.22

Assay

97%

form

liquid

optical activity

[α]25/D +7.3°, c = 2 in chloroform

refractive index

n20/D 1.483 (lit.)

density

1.461 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](CO)CBr

InChI

1S/C4H9BrO/c1-4(2-5)3-6/h4,6H,2-3H2,1H3/t4-/m1/s1

InChI key

KIBOHRIGZMLNNS-SCSAIBSYSA-N

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Application

(S)-(+)-3-Bromo-2-methyl-1-propanol is a precursor to synthesize the phase II mexiletine metabolite, (R)-mexiletine N-carbonyloxy-β-D-glucuronide. It can be used in the synthesis of (R)-(+)-muscopyridine, polycavernoside A and (+)-allopumiliotoxin 323B′. It can also be employed in building homochiral porous molecular networks.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Synthesis of (+)?Allopumiliotoxin 323B?.
Tan CH and Holmes A B
Chemistry?A European Journal , 7(9), 1845-1854 (2001)
First synthesis and full characterization of mexiletine N-carbonyloxy ?-D-glucuronide.
Cavalluzzi M M, et al.
Tetrahedron Letters, 51(40), 5265-5268 (2010)
Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid.
White J d, et al.
Journal of the American Chemical Society, 123(35), 8593-8595 (2001)
A Catalytic Approach to (R)?(+)?Muscopyridine with Integrated ?Self?Clearance?.
Furstner A and Leitner A
Angewandte Chemie (International Edition in English), 42(3), 308-311 (2003)
Control and induction of surface-confined homochiral porous molecular networks.
Tahara K, et al.
Nature Chemistry, 3(9), 714-719 (2011)

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